33141-33-2

Usage

InChI:InChI=1/C10H12N2O/c1-13-10-5-3-9(4-6-10)12-8-2-7-11/h3-6,12H,2,8H2,1H3

Upstream product

• 5351-04-2 3-diethylaminopropionitrile 
• 20265-97-8 p-anisidine hydrochloride 
• 104-94-9 4-methoxy-aniline 
• 107-13-1 acrylonitrile 
• 5198-48-1 3-(4-methoxy-phenyl)-oxazolidin-2-one 

Downstream Products

• 28461-45-2 1-(2-Cyanoethyl)-1-(p-methoxyphenyl)-harnstoff 
• 117652-36-5 ethyl N-(β-cyanoethyl)-N-(4-methoxyphenyl)glycinate 
• 117652-37-6 1-(4-methoxyphenyl)-4-oxopyrrolidine-3-carbonitrile 
• 138653-50-6 9-Methoxy-1,11-diphenyl-4,5-dihydro-3H-[1,4]diazepino[1,2-a]indole 
• 138653-35-7 9-Methoxy-1-methyl-11-phenyl-4,5-dihydro-3H-[1,4]diazepino[1,2-a]indole 
• 138653-43-7 9-Methoxy-11-methyl-1-phenyl-4,5-dihydro-3H-[1,4]diazepino[1,2-a]indole 
• 138653-18-6 3-(5-Methoxy-3-phenyl-indol-1-yl)-propylamine 
• 138653-23-3 N-[3-(5-Methoxy-3-phenyl-indol-1-yl)-propyl]-benzamide 
• 138898-62-1 3-(5-Methoxy-3-phenyl-indol-1-yl)-propionic acid 
• 81057-35-4 3-(5-Methoxy-3-phenyl-indol-1-yl)-propionitrile 

Relevant academic research and scientific papers

Synthesis and pharmacological evaluation of 3-[(4-Oxo-4H-pyrido[3,2-e][1,3]thiazin-2-yl)(phenyl)amino]propanenitrile derivatives as orally active AMPA receptor antagonists

In our search for novel orally active α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptor antagonists, we found that conversion of an allyl group in the lead compound 2-[allyl(4-methyl-phenyl)amino]-4H-pyrido[3,2-e][1,3]thiazin-4-one (4)

A green and convenient approach for the one-pot solvent-free synthesis of coumarins and β-amino carbonyl compounds using Lewis acid grafted sulfonated carbon@titania composite

Abstract: This paper reports an efficient protocol for the synthesis of coumarins via Pechmann reaction, and β-amino carbonyl compounds via aza-Michael reaction using catalytic amount of solid Lewis acid catalyst, C@TiO2–SO3–SbCl2. Six different catalysts were prepared by covalent immobilization of homogeneous Lewis acids onto sulfonated carbon@titania composite derived from amorphous carbon and nano-titania. Among various catalysts tested, C@TiO2–SO3–SbCl2 showed superior catalytic activity. The catalyst could be recycled without significant loss of its catalytic activity and demonstrated versatile catalysis for a wide range of substrates. Graphical abstract: [Figure not available: see fulltext.]

Synthesis, Characterization and Catalytic Application of MCM 41 Supported Phenanthrolinium Dibromide Catalyst for Aza-Michael Addition Reaction in Aqueous Medium

Abstract: MCM-41 immobilized phenanthrolinium dibromide (phen-MCM-Br2) was easily prepared and applied as an efficient heterogeneous catalyst for aza-Michael addition of aromatic amines to α,β-unsaturated nitriles and nitro compounds in water. The catalyst was characterized by CHN, TGA, FT-IR, SEM, EDAX, XRD, BET, and TEM. It could be simply recovered and reused several times without significant loss of catalytic activity. Graphical Abstract: [Figure not available: see fulltext.]

Copper-Catalyzed Aza-Michael Addition of Aromatic Amines or Aromatic Aza-Heterocycles to α,β-Unsaturated Olefins

A highly efficient and mild Cu-catalyzed conjugate addition reaction of aromatic amines and aromatic aza-heterocycles to α,β-unsaturated olefins is described. The transformation is promoted by 3-7 mol % of a Cu complex generated in situ from a mixture of inexpensive CuCl, a readily available phosphine or imidazolium salt, and KOt-Bu at ambient temperature. A wide range of β-amino sulfone, β-amino nitrile, and β-amino carbonyl compounds is efficiently and selectively synthesized in high yields (62-99%).

Polymer coated magnetically separable organocatalyst for C[sbnd]N bond formation via aza-Michael addition

A polyacrylamide coated magnetite (PAM@MNP) catalyst was synthesized by following a two step approach involving the reaction of magnetite (Fe3O4) particles with coupling agent 3-(trimethoxysilyl)propyl methacrylate followed by grafting of acrylamide and subsequent polymerization via surface initiated radical polymerization technique. The synthesized organocatalyst was used for a one-pot aza-Michael addition reaction of amines with electron deficient alkenes to give β-amino carbonyls. The magnetic properties of the synthesized organocatalyst provide it a facile recovery by external magnet which eliminates the problems arising during catalyst separation by conventional filtration.

The zeolite ZSM-5-SO3H catalyzed aza-Michael addition of amines and sulfonamides to electron-deficient alkenes under solventfree conditions

Aza-Micheal addition of aromatic and aliphatic amines and sulfonamides to α,β-unsaturated esters, ketones and nitriles has been developed using the zeolite ZSM-5-SO3H as catalyst under solvent-free conditions.

The zeolite ZSM-5-SO3H catalyzed aza-Michael addition of amines and sulfonamides to electron-deficient alkenes under solvent-free conditions

Aza-Micheal addition of aromatic and aliphatic amines and sulfonamides to α,β-unsaturated esters, ketones and nitriles has been developed using the zeolite ZSM-5-SO3H as catalyst under solvent-free conditions.

Chemo/regioselective Aza-Michael additions of amines to conjugate alkenes catalyzed by polystyrene-supported AlCl3

A simple and efficient procedure is presented for Aza-Michael additions of various amines with conjugate alkenes bearing electron withdrawing group catalyzed by polystyrene-supported aluminum chloride (Ps-AlCl3) without the use of any solvents. The catalyst shows high catalytic activity for both aromatic amines and aliphatic amines. Chemoselective additions of the two types of amines with conjugate alkenes are achieved. Regioselective additions of two different amino groups in one molecule proceed smoothly. Ps-AlCl 3 has better recyclability and can be reused several times without apparent loss of activity.

Selective and nonselective aza-michael additions catalyzed by a chiral zirconium bis-diketiminate complex

Reaction of the chiral bis-diketiminate complex rac- or (R,R)-C 6H10(nacnacXyl)2ZrCl2 with AgOTf yielded the corresponding bis-triflate complex. The complex geometry changes from distorted octahedral in the dichloride complex to a pseudotetrahedral coordination involving π coordination of the diketiminate ligands. The bis-triflate complex is highly active for aza-Michael additions with turnover frequencies of 20000/h for the addition of morpholine to acrylonitrile and 1000/h for the addition of morpholine to methacrylonitrile. The enantioselectivities of the latter reaction in various solvents were low, never surpassing 19% ee. The reaction is first-order in olefin concentration and second order in amine concentration, which is explained by its participation as a base in the reaction mechanism. The presence of catalytic amounts of triethylamine slightly increases the observed rate constants and reduces the reaction order in amine to first order. Other activated alkenes such as methacrylonitrile, crotonitrile, methyl acrylate, and cyclohexenone can be employed, but no reactivity is observed toward styrene or vinyl ethers. Primary amines, secondary amines, and anilines can be employed as nucleophiles with activities correlating with their nucleophilicity, but the catalyst is unstable in the presence of alcohols.

Lithium tetrafluoroborate catalyzed highly efficient inter- and intramolecular aza-Michael addition with aromatic amines

Lithium tetrafluoroborate has been demonstrated for the first time to be an efficient catalyst in intermolecular aza-Michael addition aromatic amines to electron deficient alkenes. Suitability of the same catalyst in intramolecular aza-Michael addition leading 2-aryl-2,3-dihydroquinolin-4(1H) ones has also been described.